Enantioselective construction of pyrrolidines by palladium-catalyzed asymmetric [3+ 2] cycloaddition of trimethylenemethane with imines

BM Trost, SM Silverman

Index: Trost, Barry M.; Silverman, Steven M. Journal of the American Chemical Society, 2012 , vol. 134, # 10 p. 4941 - 4954

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Citation Number: 43

Abstract

A protocol for the enantioselective [3+ 2] cycloaddition of trimethylenemethane (TMM) with imines has been developed. Central to this effort were the novel phosphoramidite ligands developed in our laboratories. The conditions developed to effect an asymmetric TMM reaction using 2-trimethylsilylmethyl allyl acetate were shown to be tolerant of a wide variety of imine acceptors to provide the corresponding pyrrolidine cycloadducts with excellent ...